52939-54-5Relevant academic research and scientific papers
Tishchenko reactions and Oppenauer oxidation reactions of aldehydes promoted by diisobutylaluminum hydride
Hon, Yung-Son,Chang, Chun-Ping,Wong, Ying-Chieh
, p. 3313 - 3315 (2004)
The aliphatic aldehydes react with catalytic amount of Dibal-H in n-pentane to give the corresponding Tishchenko products in good to excellent yields. Contrary, α-silyloxyaldehydes give α-silyloxyketones via Oppenauer oxidation under similar condition.
Tishchenko reactions of aldehydes promoted by diisobutylaluminum hydride and its application to the macrocyclic lactone formation
Hon, Yung-Son,Wong, Ying-Chieh,Chang, Chun-Ping,Hsieh, Cheng-Han
, p. 11325 - 11340 (2008/03/12)
Aliphatic aldehydes react with catalytic amount of Dibal-H in n-pentane to give the corresponding Tishchenko products in good to excellent yields. On contrary, α-silyloxy aldehydes give α-silyloxy ketones via Oppenauer oxidation under similar condition. Tishchenko reaction of ω-alkene aldehydes followed by RCM and hydrogenation affords a convenient method to prepare the 11-37 membered macrocyclic lactones.
Organometallic-type reactions in aqueous media mediated by indium. Allylation of acyloyl-imidazoles and pyrazoles. Regioselective synthesis of β,γ-unsaturated ketones.
Bryan, Vernal J.,Chan, Tak-Hang
, p. 6493 - 6496 (2007/10/03)
Indium mediated coupling of allylic bromide with acyloyl-imidazoles or pyrazoles in aqueous media gives the corresponding tertiary alcohols or ketones in good yield. The reaction provides a facile regioselective synthesis of P,β,γ-unsaturated ketones and its usefulness is demonstrated by the synthesis of the monoterpene artemesia ketone.
172. β-Cleavage of Bis(homoallylic) Potassium Alkoxides. Two-Step Preparation of Propenyl Ketones from Carboxylic Esters. Synthesis of ar-Turmerone, α-Damascone, β-Damascone, and β-Damascenone
Snowden, Roger L.,Linder, Simon M.,Muller, Bernard L.,Schulte, Karl H.
, p. 1858 - 1878 (2007/10/02)
The transformation of 36 bis(homoallylic) alcohols VII to alkenones IX and X via β-cleavage of their potassium alkoxides VIIa in HMPA has been investigated (cf.Scheme 2).These studies have established an order of β-cleavage for 2-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1,1-dimethyl-2-propenyl, and benzyl groups in alkoxides 49a-56a and have allowed a comparison between the β-cleavage reaction and the oxy-Cope rearrangement in alkoxides 74a-83a.As illustrative synthetic applications, a two-step preparation of propenyl ketones 15-42 from carboxylic esters is described, together with syntheses of ar-turmerone (48), α-damascone ((E)-71), β-damascone ((E)-109), and β-damascenone ((E)-111).
